ALLYL CROTONATE

CAS: 20474-93-5 FLAVORING AGENT OR ADJUVANT

ALLYL CROTONATE (CAS 20474-93-5) is a synthetic ester used primarily as a flavoring agent or adjuvant in food applications. It is a colorless clear liquid with distinct aroma properties and is recognized in flavor industry reference libraries such as FEMA 4072. Its use in food is as a flavor enhancer in a broad set of food product categories. Regulatory status with major agencies is not established via direct CFR listings but it appears in flavor ingredient inventories.

What It Is

ALLYL CROTONATE is a flavoring agent or adjuvant described chemically as an allyl ester of crotonic acid with the CAS number 20474-93-5. It is a clear, colorless liquid under typical conditions and is recognized by flavor industry compendia with the FEMA (Flavor and Extract Manufacturers Association) number 4072, indicating its evaluation as a flavor ingredient in the flavor industry context. It is not listed with an INS/E-number in official international additive coding schemes, and formal regulatory approvals by major food safety authorities do not appear in dedicated food additive regulations, though its inclusion in certain flavor inventories suggests it has been used historically as a flavoring substance. Its other names reflect its ester chemistry and structural synonyms that have been used in industrial and flavor science contexts.

How It Is Made

The manufacture of allyl crotonate typically involves organic esterification reactions between crotonic acid (but-2-enoic acid) and allyl alcohol under controlled acidic catalysis conditions, forming the allyl ester linkage and yielding the target compound. Such esterification is a classical approach in fine chemical synthesis, where the carboxylic acid component and alcohol are combined under catalysis with removal of water to drive the reaction. Purification steps such as distillation or chromatography are typically applied in industrial or laboratory settings to isolate allyl crotonate at high purity. Commercially available samples are often supplied with typical purity specifications suitable for flavor applications or research use, reflecting the needs of formulation scientists. The process emphasizes control of reaction conditions to minimize impurities that could impact sensory properties or regulatory evaluations.

Why It Is Used In Food

ALLYL CROTONATE is used in food as a flavoring agent or adjuvant because of its distinctive taste and aroma characteristics that can enhance or modify the sensory profile of various food products. Flavoring agents are typically incorporated in food systems at low concentrations to create desired sensory effects without contributing significant bulk or nutritional value. In the flavor industry, compendial lists such as those maintained by FEMA assign numbers like 4072 to substances that have been evaluated for flavor use, indicating common application contexts. Flavorists may choose allyl crotonate in certain formulations when a specific estery, fruity, or green aroma note is desired, complementing other flavors and contributing to overall flavor complexity. Its ester chemistry makes it compatible with other flavor compounds and suitable for use in water- and oil-based food systems when formulated correctly.

Adi Example Calculation

Because there is no authoritative, numeric Acceptable Daily Intake (ADI) value published for allyl crotonate in major public regulatory evaluations, an illustrative ADI calculation cannot be provided with a specific numeric benchmark. In contexts where ADIs are established for other additives, an example calculation might involve multiplying the ADI (mg per kg body weight per day) by a hypothetical body weight to estimate allowable daily intake; however, without a confirmed numeric ADI for this compound, such an illustration is not feasible. This reflects the regulatory reality that not all flavoring agents have publicly accessible numerical ADIs, and safety considerations instead depend on industry evaluations and use-level controls within good manufacturing practice frameworks.

Safety And Health Research

Safety evaluations for flavoring substances like allyl crotonate typically revolve around toxicological studies, assessments of chronic toxicity, genotoxicity, metabolic fate, and exposure levels relative to expected intake. Regulatory bodies and expert panels, such as those convened by FEMA, compile and review available data to inform flavor industry use recommendations. The available literature reflects its evaluation within the flavor industry context, but there is limited public-domain toxicological data detailing comprehensive safety endpoints or acceptable intake levels specific to allyl crotonate. As with many flavor esters, safety assessments take into account the levels of exposure expected from typical food use and compare those to toxicological data from laboratory studies. Because detailed quantitative safety data are not readily available in the public regulatory databases for this compound, precise hazard characterizations and benchmark values remain limited. Risk assessment for any food additive necessarily balances hazard information with exposure estimates to determine safe conditions of use.

Regulatory Status Worldwide

The regulatory status of allyl crotonate as a food additive is not directly codified in major statutory additive lists such as the U.S. Code of Federal Regulations (CFR) with a specific section that authorizes its use by name, nor is it associated with an international additive number (INS/E-number) in the Codex Alimentarius system. However, it is included in flavor ingredient inventories maintained by industry bodies such as the Flavor and Extract Manufacturers Association (FEMA), where it carries the FEMA number 4072, which reflects evaluation as a flavoring substance in the flavor industry context. Additionally, allyl crotonate appears in the U.S. Food and Drug Administration's Substances Added to Food inventory (formerly EAFUS), where flavor ingredients are indexed for informational purposes. Inclusion in these inventories suggests that it has been historically used or evaluated for use in food flavoring, but it does not constitute an explicit, regulation-based approval listing under a specific CFR section. Regulatory frameworks differ by region, and formal acceptance may be based on national risk assessments or inventories rather than prescriptive use listings.

Taste And Functional Properties

ALLYL CROTONATE typically exhibits sensory characteristics described in flavor chemistry references as having fruity, green, or estery aroma notes that contribute to desirable flavor profiles when used at appropriate levels. Ester compounds in general are valued in flavor science for their ability to impart specific sensory impressions that are recognized by consumers as pleasant or enhancing other flavor notes. In terms of functional behavior, allyl crotonate is soluble in organic solvents and must be formulated for even distribution in complex food matrices. It is generally stable under typical conditions of flavor formulation, but as with many esters, extreme heat or prolonged exposure to certain conditions could alter its sensory impact. Because it is used at low concentrations, functional considerations also include volatility and interaction with packaging and other ingredients, which formulation scientists must account for in product development.

Acceptable Daily Intake Explained

The Acceptable Daily Intake (ADI) is a risk assessment concept used by food safety authorities to express the amount of a substance that can be ingested daily over a lifetime without appreciable health risk, based on toxicological data and uncertainty factors. For substances like allyl crotonate where specific ADI values have not been established in authoritative food additive evaluations accessible in public regulatory databases, it is not possible to assign a numeric ADI. The absence of a defined ADI in public records means that any assessment of safe intake would rely on broader flavor industry evaluations, such as FEMA's expert panel conclusions, rather than explicit quantitative ADI statements. In general, when ADIs are established for flavoring agents, they reflect conservative assumptions about long-term exposure and incorporate safety margins to protect consumers across populations.

Comparison With Similar Additives

ALLYL CROTONATE can be compared with other estery flavoring agents such as ethyl butyrate and methyl butyrate, which are also used for fruity or estery sensory notes in food products. Ethyl butyrate is commonly perceived as contributing pineapple or fruit-like aroma, while methyl butyrate imparts apple or fruity nuances; allyl crotonate contributes distinct green or complex estery notes that may complement these other esters. In formulation practice, flavorists blend multiple esters and volatile compounds to achieve target sensory profiles, selecting each based on odor threshold, volatility, and compatibility. Unlike some more common esters that have well-defined regulatory ADIs and explicit listing in additive regulations, allyl crotonate’s use is primarily guided by industry inventory inclusion and flavor industry expertise. This underscores both functional similarities with other esters and regulatory distinction in the level of public quantitative safety data available.

Common Food Applications Narrative

ALLYL CROTONATE finds application in a variety of flavor formulations across broad food categories because of its distinctive aroma contributions. In baked goods, such as cookies and pastries, estery flavor notes can complement sweet and buttery profiles. Breakfast cereals and snack products often incorporate flavoring esters to enhance fruit or cereal grain impressions. In dairy and frozen dessert applications, such flavoring agents help round out complex flavor profiles when natural ingredients alone may not provide the desired sensory impact. Beverages, including nonalcoholic soft drinks and fruit-flavored drinks, may use small amounts of flavoring esters to convey freshness or fruit-like qualities. Condiments, sauces, and confectionery items also leverage the unique sensory properties of allyl crotonate in blended flavor systems. The narrative across these applications is that allyl crotonate supports overall sensory perception in foods where subtle, nuanced flavor contributions are critical in creating appealing products for consumers.

Safety & Regulations

FDA

  • Notes: No specific FDA CFR section authorizing allyl crotonate by name could be found in public regulatory listings; it is indexed in flavor ingredient inventories without explicit numeric regulatory listing.

EFSA

  • Notes: No EFSA additive approval or ADI listing was identified in authoritative public sources.

JECFA

  • Notes: JECFA has not published a publicly accessible ADI or explicit evaluation entry with numeric values for this compound.

Sources

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